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Lindahl U, Li JP, Kusche-Gullberg M, Salmivirta M, Alaranta S, Veromaa T, Emeis J, Roberts I, Taylor C, Oreste P, Zoppetti G, Naggi A, Torri G, Casu B
Generation of 'neoheparin' from E. coli K5 capsular polysaccharide
Journal of Medicinal Chemistry 48(2) (2005)
349-352
Escherichia coli K5
(Ancestor NCBI TaxID 562,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
NCBI PubMed ID: 15658847Journal NLM ID: 9716531Publisher: Washington, DC: American Chemical Society
Correspondence: ulf.lindahl
imbim.uu.se
Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Box 582, SE-751 23 Uppsala, Sweden
Heparin remains a major drug in prevention of thromboembolic disease. Concerns related to its animal source have prompted search for heparin analogues. The anticoagulant activity of heparin depends on a specific pentasaccharide sequence that binds antithrombin. We report the generation of a product with antithrombin-binding, anticoagulant, and antithrombotic properties similar to those of heparin, through combined chemical and enzymatic modification of a bacterial (E. coli K5) polysaccharide. The process is readily applicable to large-scale production.
capsular polysaccharide, Escherichia coli, heparin, chemical synthesis, anticoagulant activity, enzymatic modification
Structure type: polymer chemical repeating unit
Location inside paper: p.349
Trivial name: K5 polysaccharide, K-antigen, N-acetyl heparosan, heparosan (N-acetylheparosan), heparosan, heparosan (glycosaminoglycan GAG), K5 CPS, heparosan (K5-antigen), N-acetylheparosan
Compound class: EPS, K-antigen, CPS, polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_141807,IEDB_151531,IEDB_153764,IEDB_423153
Methods: biological assays, biosynthetic modifications, chemoenzymatic modifications
Related record ID(s): 10798
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G26089XS, GlycomeDB:
656
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Lindahl U, Li JP, Kusche-Gullberg M, Salmivirta M, Alaranta S, Veromaa T, Emeis J, Roberts I, Taylor C, Oreste P, Zoppetti G, Naggi A, Torri G, Casu B
Generation of 'neoheparin' from E. coli K5 capsular polysaccharide
Journal of Medicinal Chemistry 48(2) (2005)
349-352
|
S-6)-+
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S-6)-+ S-2)-+ | S-2)-+ S-2)-+
| | | | |
-4)-a-D-GlcpNAc-(1-4)-b-D-GlcpA-(1-4)-a-D-GlcpN-(1-4)-a-L-IdopA-(1-4)-a-D-GlcpN-(1-
| |
S-3)-+ S-6)-+ |
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Escherichia coli K5
(Ancestor NCBI TaxID 562,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 ]
NCBI PubMed ID: 15658847Journal NLM ID: 9716531Publisher: Washington, DC: American Chemical Society
Correspondence: ulf.lindahl
imbim.uu.se
Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Box 582, SE-751 23 Uppsala, Sweden
Heparin remains a major drug in prevention of thromboembolic disease. Concerns related to its animal source have prompted search for heparin analogues. The anticoagulant activity of heparin depends on a specific pentasaccharide sequence that binds antithrombin. We report the generation of a product with antithrombin-binding, anticoagulant, and antithrombotic properties similar to those of heparin, through combined chemical and enzymatic modification of a bacterial (E. coli K5) polysaccharide. The process is readily applicable to large-scale production.
capsular polysaccharide, Escherichia coli, heparin, chemical synthesis, anticoagulant activity, enzymatic modification
Structure type: polymer chemical repeating unit
Location inside paper: p.350, Fig. 1
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_141807,IEDB_142354,IEDB_151531,IEDB_241120,IEDB_241121,IEDB_423153
Methods: biological assays, biosynthetic modifications, chemoenzymatic modifications
Biological activity: antithrombin-binding, anticoagulant activities, antithrombotic activities
Comments, role: modified capsular polysaccharide
Related record ID(s): 10573
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G01715ML, GlycomeDB:
27829
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Richard E, Buon L, Drouillard S, Fort S, Priem B
Bacterial synthesis of polysialic acid lactosides in recombinant Escherichia coli K-12
Glycobiology 26(7) (2016)
723-731
Escherichia coli K1
(NCBI TaxID 1392869,
species name lookup)
Escherichia coli K92
(Ancestor NCBI TaxID 562,
species name lookup)
Neisseria meningitidis
(NCBI TaxID 487,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 ];
infection due to Neisseria meningitidis [ICD11:
XN1DV ]
NCBI PubMed ID: 26927318Publication DOI: 10.1093/glycob/cww027Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: Bernard.Priem
cermav.cnrs.fr
Institutions: Univ. Grenoble Alpes, CERMAV, F-38000 Grenoble, France CNRS, CERMAV, F-38000 Grenoble, France
Bacterial polysialyltransferases (PSTs) are processive enzymes involved in the synthesis of polysialic capsular polysaccharides. They can also synthesize polysialic acid in vitro from disialylated and trisialylated lactoside acceptors, which are the carbohydrate moieties of GD3 and GT3 gangliosides, respectively. Here, we engineered a non-pathogenic Escherichia coli strain that overexpresses recombinant sialyltransferases and sialic acid synthesis genes and can convert an exogenous lactoside into polysialyl lactosides. Several PSTs were assayed for their ability to synthesize polysialyl lactosides in the recombinant strains. Fed-batch cultures produced α-2,8 polysialic acid or alternate α-2,8-2,9 polysialic acid in quantities reaching several grams per liter. Bacterial culture in the presence of propargyl-beta-lactoside as the exogenous acceptor led to the production of conjugatable polysaccharides by means of copper-assisted click chemistry.
capsular polysaccharide, polysialic acid, bacterial glycosylation, Escherichia coli K12, click chemistry, glyco-engineering
Structure type: homopolymer
Location inside paper: p.723
Trivial name: polysialic acid
Compound class: CPS
Methods: 13C NMR, 1H NMR, DNA sequencing, TLC, genetic methods, HPAEC-PAD, chemoenzymatic modifications, conjugation
NCBI Taxonomy refs (TaxIDs): 1392869,
562,
487Reference(s) to other database(s): GTC:G89228EH, GlycomeDB:
27240
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